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Crocin

suitable for microscopy

Sinónimos:

Crocetin digentiobiose ester

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Fórmula empírica (notación de Hill):
C44H64O24
Número CAS:
42553-65-1
Peso molecular:
976.96
NACRES:
NA.47
PubChem Substance ID:
57647630
UNSPSC Code:
12352200
EC Number:
255-881-6
MDL number:
MFCD00017495
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form

solid

Quality Level

100

suitability

suitable for microscopy

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

CC(=C\C=C\C=C(C)\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)\C=C\C=C(\C)C(=C)CO[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O

InChI

1S/C46H68O23/c1-21(12-8-14-23(3)25(5)18-62-43-40(59)36(55)32(51)28(67-43)19-63-44-38(57)34(53)30(49)26(16-47)65-44)10-6-7-11-22(2)13-9-15-24(4)42(61)69-46-41(60)37(56)33(52)29(68-46)20-64-45-39(58)35(54)31(50)27(17-48)66-45/h6-15,26-41,43-60H,5,16-20H2,1-4H3/b7-6+,12-8+,13-9+,21-10-,22-11+,23-14-,24-15+/t26-,27-,28-,29-,30-,31-,32-,33-,34+,35+,36+,37+,38-,39-,40-,41-,43-,44-,45-,46+/m1/s1

InChI key

LUVDBMJRTUBHNX-RSXXRLSLSA-N

General description

A highly unsaturared diterpene dicarboxylic acid ester found in saffron.
Crocin (CR) is a water-soluble carotenoid found in Gardenia jasmi-noides Ellis and Crocus sativus (saffron). It has two D-gentiobioside glycosyl esters in its structure. CR is one of the major bioactive compounds of saffron contributing to its red color.

Application

Crocin has been used:
  • as a reference standard to detect its presence in Crocus sativus L. extract using high-performance liquid chromatography technique
  • to investigate its protective effects as an antioxidant and anti-inflammatory agent against doxorubicin-induced nephrotoxicity in rats
  • to test antitumor effects and its role in promoting autophagy and apoptosis and inhibiting the progression of cervical cancer on SiHa cells and female BALB/c nude mice
  • as a co-treatment with cisplatin to test its protective effect against cisplatin (CIS)-induced testicular toxicity in rats

Biochem/physiol Actions

Crocin alleviates some ethanol-induced impairments of learning and prevents ethanol-induced inhibition of hippocampal long-term potentiation (LTP), a form of activity-dependent synaptic plasticity that may underly learning and memory. Related CNS effects are specific to the digentiobiose ester; crocetin glucose gentiobiose ester is half as potent, and the diglucose ester has no effect at all.
Crocin exerts antioxidant, anti-inflammation, anti-cancer, antidegenerative, and antidiabetic properties.

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Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
BCCP2238
BCCN9373
BCCG1963
BCCK6052
BCCD4237

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Francesca Gullo et al.
Frontiers in neuroscience, 11, 500-500 (2017-09-22)
Increasing evidence supports a decisive role for neuroinflammation in the neurodegenerative process of several central nervous system (CNS) disorders. Microglia are essential mediators of neuroinflammation and can regulate a broad spectrum of cellular responses by releasing reactive oxygen intermediates, nitric
Olga Bountagkidou et al.
Journal of chromatography. A, 1237, 80-85 (2012-03-31)
An on-line HPLC (high performance liquid chromatography) method for the rapid screening of individual antioxidants in mixtures was developed using crocin as a substrate (i.e. oxidation probe) and 2,2'-azobis(2-amidinopropane dihydrochloride (AAPH)) in phosphate buffer (pH 7.5) as a radical generator.
Mika Masaki et al.
Molecular nutrition & food research, 56(2), 304-308 (2011-11-01)
Crocus sativus L. (saffron) has been traditionally used for the treatment of insomnia and other diseases of the nervous systems. Two carotenoid pigments, crocin and crocetin, are the major components responsible for the various pharmacological activities of C. sativus L.
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